


1927

by victoriagreen



Category: Supernatural
Genre: Alternate Universe - 1920s, Bartender!Cas, Circus, Eventual Smut, F/M, Fluff and Angst, Homophobia, Italian Mafia, M/M, Period-Typical Homophobia, Prohibition, detective!dean, speakeasy
Language: English
Status: In-Progress
Published: 2015-09-24
Updated: 2015-10-18
Packaged: 2018-04-23 04:56:30
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, Graphic Depictions Of Violence
Chapters: 4
Words: 3,594
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4863959
Author URL: https://archiveofourown.org/users/victoriagreen/pseuds/victoriagreen
Summary: <blockquote class="userstuff">
              <p>Detective Dean Winchester has always been the force's best man for infiltrating saloons and speakeasies. He was charming, and made friends quickly. On his last raid, he meets a bartender with fierce eyes and an awe-inspiring smile, and has no choice but to flee from his coworkers with the stranger, to save them both from prison. But where can they go now that Chicago's dirtiest are searching for them?</p>
            </blockquote>





	1. The Last Raid

**Author's Note:**

> Leave a comment/kudos/constructive criticism! I wrote this chapter this morning, because I am obsessed with this time period. HUGE things to come, *spoiler* (if you like 1920's-30's circuses and mob dramatics). Enjoy!

“Winchester! Up and at ‘em, we’ve got a party to crash, boy! Get moving!” A swift kick against the chair finally roused Dean from where he’d been dozing on his desk. How he ever fell asleep is beyond him, with the stench of cigar smoke heavy in his nostrils and the men of the station loudly boasting about the raids they’d successfully carried out the nights before.

The year was 1927, with the prohibition in full swing, and Detective Dean Winchester was quite the busy man. He leaned backwards against his wooden chair and pushed away from the huge desk, covered in parchment and folders of other cases, cigarette butts, and the brown sack from his lunch earlier.

“Winchester, are you even fucking hearing me? Get out of here. 9th and Charleston. We’ll meet you there at 11:15 sharp, get in the thick of things. This is a big one.” Police Chief Singer nudged against his arm with a small flask, “to get your mind right.” Of course Singer would have moonshine, but Dean took a pull anyways. Leave it to the authorities to break their own rules. Fucking hypocrites.

It was already 9:45, so Dean pulled his suit coat over his slightly wrinkled white shirt and smoothed his tie down. “Hold it down, boys. See you all real soon,” he winked as he turned to the hat rack next to the door and swung his grey fedora down to land on his head. As he pulled the door open, he reached into the pockets of his slacks to retrieve a cigarette and headed to 9th and Charleston.

This speakeasy, which the patrons called the Blind Tiger, wasn’t easy to find, unless you knew what you were looking for. Dean had been told to walk the street on 9th, and turn right up Charleston. On the north side of the street, there was a tobacco shop, which seemed busy enough for a Saturday evening. Asking simply for the Blind Tiger would get him caught, so he walked in and asked for a dozen long cut cigars, saying he’d tip him extra to leave one out to smoke. 

At this, the man behind the counter nodded and jerked his head to the left, pointing Dean to a powder room. He’d been told to pull the chain next to the john, which swung the wooden panel between the sink and toilet into the hidden room, and as he did so, a party in full swing greeted him.

His job was to infiltrate the underground clubs, make friends with bartenders and patrons alike, to have the alcohol flowing, and to shut down all exits so that his crew could once again fill the cells at the local jail with lawbreakers, as well as shut down some of Chicago's dirtiest alcohol rings.

Dean sidestepped two woman pulling on cigarettes through long, bejeweled holders seated on velvet cushions with high wooden backs. He meandered through the crowd, head pounding, damnit he was getting too old to have this part of the job. He wanted to come in later, when he didn’t have to deal with the crowd, the music, and the endless clouds of cigarette smoke.

Reaching the bar, he found a stool empty and sat, taking his hat off and laying it on the bar to his right. He shook another cigarette from the pack in his pockets and asked the tender the time. “10:09 sir”, he said merrily, pouring a shot of something dark for Dean, who reached for it slowly, knowing he was allowed one drink on these jobs, to keep up the air of easy-going speakeasy frequenter.

He sipped and looked to his left, where a lovely, petite woman danced on a small circular stage in a red fringe costume, feathers sticking up from her bouncing blonde ringlets. She danced and shook her hips, closing her eyes and smiling brilliantly. He could tell she was having fun, even though she was being paid to look happy. She opened her eyes and glanced at him, flashing another smile his way. He blushed, and returned his gaze to his drink, turning back to the bar. 

There was a good bit going on, and Dean was content to sit back and watch the scene unfold, as the customers drank more and more, dancing like loons and swinging each other around carelessly.

Suddenly a small, hidden door at the back of the bar opened, catching Dean's attention, and a black-haired man with a beautiful dark blue suit stepped through. He removed his matching blue hat and hung it on a hook by the door, and he greeted the other bartender enthusiastically.

“Castiel! Wondered when you’d get here. Help me out, move these boxes of shine to that side if you could.” The other bartender shook his hand, and pointed with the other one to the couple of cases of booze he’d been referencing.

Dean's eyes followed the guy, Castiel, unsure of the reason that this enticing man had captured his mind so readily. Then, he realized, Castiel was the name of the bartender who circulated the city after raids. When one bar got shut down, he always slipped away, and moved to another bar. He was charismatic, attractive, and always flirtatious. He'd been in the alcohol ring for years, with no police ever actually laying eyes on the man.

Castiel turned to the boxes that the other bartender had referenced and swiftly moved them where the other had asked for them to be. He grabbed a bottle, cracked it open, and filled the glasses sitting on the bar to Dean's left, working his way down the bar and greeting certain customers Dean assumed had to be regulars. When he reached Dean, he slowed, his eyes narrowing, but shining brightly.

Dean could feel his face warming, but had no idea why, besides the anxiety he had begun to feel about arresting one of the city's scariest and most elusive crime ring members.

Castiel flashed a quick smile, and asked, “More, sir?” Dean held up a hand, throwing back the rest of his drink. “Alright, now, go ahead and fill me up.” The corners of his mouth quirked up. Where the fuck was this coming from? He was allowed one drink per raid, but if having another would keep the man with the blue eyes near him, hell if he would start following rules tonight.

Castiel poured him another shot, and leaned forward, “Never seen you in here handsome. What’s ya name?” He sat the bottle down and continued to stare at Dean with those piercing eyes.

“Uh, Winchester. Dean. Friend recommended I come by and,” he didn’t really know what to say. For the first time in his life, he was flustered over a man. Castiel stuck a hand over the bar, “Castiel”. Dean took the offered hand, which squeezed his gently, and lingered far too long for the public. 

Dean dropped his hand and snatched his drink up again. “Say, Castiel, would you mind telling me the time?” He needed to know when this shindig would get on the road. “it’s 10:45, sir.” Castiel picked up the bottle and poured more liquid into Dean’s glass, forcing Dean to remember why he was even there. 

Shit. Shit shit shit. He was supposed to be arresting all of these people in less than half an hour. Dean pulled another cigarette from his pocket, and looked back towards Castiel, who had moved and was currently serving the couple to his right. Castiel’s eyes flicked back to meet his, a slight smile on his lips, and Dean couldn’t help but feel a tangible cord of tension between them, though he couldn’t figure out why.

He lit his cigarette with a match from his pocket and took a drag, sparing glances at the alluring bartender, trying to get his head straight.

He’d heard that men got together sometimes, but he’d never seen it, or known anybody who swung that way personally. He’d always been a heartthrob amongst the ladies in town, but sex was simpler than feelings for him, as he worked too much. He’d never felt something quite like this tension and apparently Castiel could feel it too, because as he moved up the bar serving guests and collecting money, he continued glancing back towards Dean.

He would never have to deal with this man personally again, so what the hell, why not enjoy it?

When Castiel finally returned to Dean’s part of the bar, he made to reach for Dean’s glass and Dean subtly caught his hand, taking another pull on his cigarette. The blues flicked towards him, surprised, and Dean squeezed gently before letting go, “Where you from, blue eyes?”

Castiel’s eyebrow’s raised humorously, and that ghost of a shy smile returned. “Chicago born and bred, my man.” He leaned on his elbow against the bar, facing Dean. At that moment, the band’s leader, a dark skinned man with a huge smile, loudly announced the time, and asked somebody to bring the band members drinks, to keep up their good spirits, “It is just after eleven, and we haven’t had a drink in a while, if the kind folks of this club would replenish ours, we’d be ever so grateful, and here comes the big jam!”

He turned his back on the crowd and waved his arms dramatically. The band began playing a furiously fast-paced ragtime number, the men in the crowd pulling ladies to their feet and swinging them around.

Dean’s stomach dropped. Just after eleven. “Fuck.” He swore under his breath, and Castiel frowned and squinted at him. “You alright, Dean?” Dean looked around wildly, and turned to Castiel, “Can you trust me?” He had no idea what he was doing, but the realization hit him that he would never talk to this man again, unless he did what he felt he needed to do. 

Castiel looked at him like he was a madman, “what?” “I’m serious. We need to leave.” 

Castiel scoffed and leaned away from the bar, eyebrows quirked in interest, “I just started my shift, buddy. I can’t leave.” Dean stood and pulled his hat on, “Castiel. We. Need. To. Leave.” Castiel’s look turned icy and he stilled. 

“You’re fucking kidding me. You?” Dean shook his head and drained the last drops of his shot, pushing it to one side. “Not kidding.” He swiftly slid over the bar, to the shock of the people sitting near him, and dropped to the floor next to Castiel. 

All of a sudden, a loud banging came from upstairs in the tobacco shop and every head in the place looked to the entrance. He heard arguing, and yelling from above, glass smashing. Then the sirens, and the door from the powder room swung open harshly. 

Dean turned his head, snagged Castiel’s hat off the hook, and grabbed the other man’s hand, pulling him for the door behind the bar. He could hear people screaming and running, tables toppling as people tried to force their way out, but the police had them cornered. Men smashed small basement windows and lifted their dates out. It was mayhem. 

Castiel darted in front of Dean, pulled his hat on, and never let go of the other man’s hand.


	2. Chapter 2

**Notes for the Chapter:**

> Short chapter, I'm out of town, but next chapter will get everything moving. It's a weird time period, and homosexuality is extremely rare. We'll see where that gets them :)

Castiel pulled a thoroughly confused Dean quickly along a dark, narrow, stone hallway, until finally they were climbing a short flight of stairs, both out of breath. Castiel knocked on a small wooden door (just big enough for them to fit through without being uncomfortable) and it was opened by a burly man in an apron.

“Castiel, son, you okay? Who this is? The fuck’s happ’nin?” The man said around the cigar he was chewing. They squeezed through, and Dean watched as the door slid seamlessly into the wall behind the glass counter. Dean cast his eyes around and noticed they were in a dark butcher’s shop. The man in the apron must live above it.

“Raid, customers, everybody else gone.” Cas explained breathlessly. He pointed to his companion, “Dean”, they were still trying to catch their breath. 

“Alright, fine to stay here for a bit, but I can guess they’ll be lookin’ for ya soon, Castiel. Git a plan together and git on the road.”

Castiel nodded and the butcher went into the back room, and they could hear him climbing stairs. He pulled Dean to sit at some chairs behind the bar, out of sight of the street and dropped his hand, which he forgot he'd still been holding, it just felt natural to have such a tender warmth against his palm.

“Explain. Now.” He directed his attention at Dean, his eyes dark, but almost humoured.

Dean’s eyes widened, goddamnit what could he say to explain himself? Castiel just stared at him and leaned back against the wall, those eyes piercing into Dean’s own, his legs crossed comfortably.

“I know you’re on the force. What do you think you’re doing?”

Dean shook his head, still feeling the effects of the liquor Castiel had been pouring him earlier. “Man, I don’t know. I just couldn’t..” he broke off, looking at Castiel, hoping he had felt any of the energy between them.

Castiel’s eyes softened and leaned forward and rested his forearms on his knees, “What, Dean? Why?”

Dean exhaled slowly, trying to wrangle his thoughts. “Cas, I don’t know whats going on. But I couldn’t just let you get arrested. I know who you are, and letting you get arrested just didn't feel right.” He rested his face in his hands, and tried to decide his next move. At this point, the police had probably retrieved all of the bootlegged alcohol and arrested everyone they were looking for. Except this bartender, who he knew they’d love to get their hands on.

He felt a gentle pull on his coat sleeve, and looked up to meet tender blue eyes. 

“I don’t know either, but I’m grateful, Dean. I like Cas, by the way.” He said with a shy smile. “We probably need to make a move though, because now they’ll be after both of us. We know too much.” He laughed.

Dean rubbed his face and chuckled softly, “You’re right. Alright, gameplan.” He stood and grabbed Castiel’s hand and pulled him to his feet, never releasing his hold. “Do you trust me?” he smirked.


	3. The Train

**Notes for the Chapter:**

> The boys are so cute. I love to dangle it in front of you, because I've been told it's going too slow, (it's 1927, what do you expect?), but I love every drop of feedback I'm given. Keep holdin' on :)

The pair ran the opposite way Dean had come from, and continued north up Charleston Street, never releasing each other’s hands. Each knew it was wrong on some level, but it felt so fucking right. 

The sirens had died down, and the tobacco shop that lead to the Blind Tiger had been closed up by the police, so they just kept running, with no thought about what they might be leaving behind. Dean knew that the entire force would be searching for him, and knew that when they found out he was the reason that Castiel Novak had gotten away, they’d be after the both of them in a heartbeat.

After running as quickly as they could and seeing next to no one, besides a few of the homeless Chicago had to show, they finally slowed and caught a breath. Castiel knew they were close to the train tracks, because he’d always had to know just how far he might have to run in an emergency. 

When they neared the train tracks, Dean pulled up short. He knew this was the only way for them to escape the inevitable, but goddamn if he would hop on without any further thought. He ran his hands through his hair, hat in the other.

“Uh, Castiel, please don’t get me wrong, but is this it? Is this the only option?” He knew that train-hopping was considered the lowest of the low, the one option criminals had to save their own necks. Then he realized that he would risk everything that he had to save this blue-eyed stranger that had pulled him along for almost ten blocks now.

This was his only option. So he took a chance and pulled Castiel closer, saying “nevermind. I don’t want to know what other options there are.” Castiel seemed surprised, then tucked into Dean’s chest, pulling the lapels of his coat as close as he could.

As Castiel melted into the other man’s body, Dean closed his eyes, resting his chin on top of the shorter man, and realized this was where he needed to be right now. Not a police station, writing up an arrest record for the person in his arms. Castiel’s face was tucked against his neck, arms around his waist rather tightly for how odd the entire situation was, and Dean knew they were both extremely aware of the danger that faced them. 

The two stayed wrapped up together, until a bright light and deafening horn rounded the corner, causing them to jump apart as they realized a train was quickly approaching.

“Dean! We gotta catch this one. D’ya trust me?” Castiel smirked, grabbing Dean’s hand and pulling it to his lips to swiftly press them against the tan skin. 

Dean’s heart couldn’t have hammered any more loudly than it was at that moment. He nodded, as Castiel began to run in the direction that the train would soon be passing them. Bewildered, Dean was pulled along with Castiel, and began running along behind him as the train neared them steadily.

Dean let go of Castiel’s hand, and the two ran hard as the train’s cars passed them by quickly. Dean couldn’t see anything inside the cars besides darkness, and he began to grow even more nervous, realizing what they’d be doing. 

He couldn’t even watch where he placed his feet as he tried to keep up with Castiel and the train, and all of the sudden, Castiel swung up and into a train car ahead of Dean. Dean realized there was a handle, and Castiel was yelling to him, laying on his stomach in the train car, reaching for him, and Dean tried his best to increase his speed, without paying attention to where his feet were placed.

He felt himself falling forward as he tripped on a misplaced railroad tie, and his heart leapt into his throat as the realization hit him that he would either be hit by the train or be caught by his former coworkers, as two sets of hands landed on his forearms, dragging him upwards.

Squeezing his eyes closed tightly, he felt himself lifted painfully off of the ground, though he knew he’d been near the train car. As his back hit a wooden floor hard, he dared to open his eyes and saw the most incredible smile and shining blue eyes he’d seen his lifetime directly above his face, and he couldn’t help but grab the man and pull him down to meet his lips, squeezing him to his chest and not caring any longer about what this meant. It meant everything.

Castiel seemed shocked, almost resistant, but within seconds he had leaned into Dean’s embrace and kissed him fiercely in return, laying on the floor of a dirty train car, surrounded by strangers that apparently neither of them cared about.


	4. Chapter 4

**Summary for the Chapter:**

> I'm so sorry this is so short, and that I haven't updated in so long. It's been a crazy few weeks, but hopefully this little tidbit will help get me back into my groove. Enjoy, and as always, drop a comment & kudos! :)

Castiel finally broke away and smiled down at Dean, whose eyes shined brightly and searched Castiel’s face like he couldn’t get enough. 

“You birds gonna get up or roll in the hay all night?” a southern drawl roused them from their little world, and Castiel pushed himself to his feet, pulling Dean with him. Dean looked around to see four shadowed people, three of whom were standing and one body still seated against the opposite wall. 

The person sitting down flicked a lantern on by their feet, lighting the car up, and said, “You guys are adorable. Let’s hear some names! I’m Charlie.” She pulled her long, red hair atop her head and pinned it there. Dean blushed at her comment, rubbing a hand against the back of his neck, and Castiel chuckled and leaned against the far wall, pulling a cigarette from his pocket.

The door to the train car slid shut loudly, and the man who’d pushed it said in the thick drawl, “Benny. Come on, relax. We ain’t gonna bite ya.”

Castiel lit the cigarette and took a puff, before saying, “I’m Castiel, this is Dean.”

One of the other men in the car leaned forward with a hand out towards Castiel, and said, “Gordon. Where you boys headed?”

Castiel shook the offered hand and pulled the cigarette from between his lips with his left, “Anywhere. Needed a quick getaway, and thanks for providing.” Charlie laughed out loud, “What in the world kind of trouble did you two get yourselves into?”

Dean and Castiel looked to each other and burst into nervous laughter, and Castiel ran a hand through his hair. “Easier not to say, Charlie. Where is this train bound?”

“St. Louis. Next show’ll be there.” Charlie said.

“Show?” Dean snagged the cigarette from Castiel’s lips and brought it to his own, just to give himself something to do.

“Yeah, show. Did you not read the side of the train before you dragged your ass onto it?” Benny replied. 

Castiel looked to Dean, whose eyebrows lifted, and said, “No, we didn’t happen to catch that bit. Why, did we hop onto a circus car?” Dean snickered, as hopping aboard a circus train was a running joke at the station. Nobody ever came back from a circus train.

“You sure did, son! Welcome to the Campbell Brothers circus pal.”


End file.
